NPASS Compound

Structure

NPC185404 OpenBabel07101718292D 32 34 0 0 1 0 0 0 0 0999 V2000 -5.4899 -1.6551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2111 3.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4899 0.0770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9899 -0.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9899 -0.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0519 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1859 -0.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0519 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1859 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4899 0.0770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9021 2.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9899 0.9430 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4899 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4899 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 2.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.9899 2.6750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1420 2.8968 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 2.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7601 -0.2788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9899 0.9430 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9021 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 13 1 0 0 0 0 3 30 1 0 0 0 0 4 31 1 0 0 0 0 5 6 1 0 0 0 0 6 12 2 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 14 2 0 0 0 0 11 14 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 15 12 1 6 0 0 0 15 16 1 0 0 0 0 15 30 1 0 0 0 0 16 17 1 0 0 0 0 16 25 1 6 0 0 0 17 32 1 0 0 0 0 18 26 2 0 0 0 0 19 27 2 0 0 0 0 20 22 1 1 0 0 0 20 23 1 0 0 0 0 20 28 1 0 0 0 0 21 22 1 0 0 0 0 21 24 2 0 0 0 0 21 29 1 0 0 0 0 22 18 1 1 0 0 0 22 32 1 0 0 0 0 23 19 1 6 0 0 0 23 24 1 0 0 0 0 23 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	445.17
Volume:	440.922
LogP:	2.276
LogD:	0.63
LogS:	-3.332
# Rotatable Bonds:	8
TPSA:	128.23
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.338
Synthetic Accessibility Score:	5.393
Fsp3:	0.478
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.321
MDCK Permeability:	2.981500256282743e-05
Pgp-inhibitor:	0.116
Pgp-substrate:	0.356
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.046

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.486
Plasma Protein Binding (PPB):	83.49281311035156%
Volume Distribution (VD):	1.77
Pgp-substrate:	14.199423789978027%

ADMET: Metabolism

CYP1A2-inhibitor:	0.012
CYP1A2-substrate:	0.948
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.848
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.023
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.116
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.727

ADMET: Excretion

Clearance (CL):	6.27
Half-life (T1/2):	0.205

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.288
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.063
Rat Oral Acute Toxicity:	0.624
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.209
Carcinogencity:	0.174
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.125

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC185404

Natural Product ID:	NPC185404
*Common Name:**	11-O-Methylpseurotin A
IUPAC Name:	(5S,8S,9R)-8-benzoyl-9-hydroxy-2-[(Z,1S,2S)-1-hydroxy-2-methoxyhex-3-enyl]-8-methoxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
Synonyms:
Standard InCHIKey:	BSXLPZRKEPWAAT-CHZVKGAWSA-N
Standard InCHI:	InChI=1S/C23H27NO8/c1-5-6-12-15(30-3)16(25)17-13(2)18(26)22(32-17)20(28)23(31-4,24-21(22)29)19(27)14-10-8-7-9-11-14/h6-12,15-16,20,25,28H,5H2,1-4H3,(H,24,29)/b12-6-/t15-,16-,20+,22+,23+/m0/s1
SMILES:	CC/C=C[C@@H]([C@@H](C1=C(C)C(=O)[C@]2([C@H]([C@](C(=O)c3ccccc3)(N=C2O)OC)O)O1)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL400075
PubChem CID:	23656807
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003670] Aryl ketones [CHEMONTID:0004296] Phenylketones [CHEMONTID:0004298] Alkyl-phenylketones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17616609]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17929896]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19113967]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19159274]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19256529]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	isolated from sediment collected using a hand held deep water sampling device at >33 m depth in Vanuatu	2003	PMID[20303767]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667925]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21954885]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22106303]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	stem bark of Melia azedarach	n.a.	n.a.	PMID[22409377]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23557488]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23563483]
NPO41356	Aspergillus fumigatus MR2012 + Streptomyces leeuwenhoekii strain C34	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[28744271]
NPO41357	Aspergillus fumigatus MR2012 + Streptomyces leeuwenhoekii strain C34/strain C58	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[28744271]
NPO41365	Aspergillus sulphureus + Isaria felina	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[29884864]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7622436]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10538	Aspergillus fumigatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	2

Activity Type	# Activity
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IZ	=	4.0	mm	PMID[502987]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IZ	=	9.0	mm	PMID[502987]
NPT2	Others	Unspecified		IC50	>	10000.0	nM	PMID[502988]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC185404 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	212
0.1-0.2	830
0.2-0.3	3157
0.3-0.4	8890
0.4-0.5	13687
0.5-0.6	14286
0.6-0.7	1608
0.7-0.8	18
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9856	High Similarity	NPC339338
0.9856	High Similarity	NPC146097
0.9856	High Similarity	NPC227905
0.8857	High Similarity	NPC477680
0.7483	Intermediate Similarity	NPC236405
0.7432	Intermediate Similarity	NPC81135
0.7161	Intermediate Similarity	NPC208725
0.7097	Intermediate Similarity	NPC113325
0.7097	Intermediate Similarity	NPC279045
0.7089	Intermediate Similarity	NPC111586
0.7089	Intermediate Similarity	NPC108852
0.7089	Intermediate Similarity	NPC261709
0.7083	Intermediate Similarity	NPC188010
0.7063	Intermediate Similarity	NPC49565
0.7051	Intermediate Similarity	NPC472247
0.7039	Intermediate Similarity	NPC116057
0.7032	Intermediate Similarity	NPC228511
0.7006	Intermediate Similarity	NPC473055
0.7006	Intermediate Similarity	NPC473052
0.6986	Remote Similarity	NPC471553
0.6971	Remote Similarity	NPC315406
0.6968	Remote Similarity	NPC328070
0.6962	Remote Similarity	NPC322526
0.6962	Remote Similarity	NPC471201
0.6959	Remote Similarity	NPC105709
0.6948	Remote Similarity	NPC183722
0.6933	Remote Similarity	NPC65627
0.6928	Remote Similarity	NPC472707
0.6918	Remote Similarity	NPC108532
0.6914	Remote Similarity	NPC237240
0.6914	Remote Similarity	NPC31171
0.6906	Remote Similarity	NPC471395
0.6885	Remote Similarity	NPC67246
0.6885	Remote Similarity	NPC33372
0.6867	Remote Similarity	NPC160493
0.6864	Remote Similarity	NPC476194
0.6852	Remote Similarity	NPC45307
0.6842	Remote Similarity	NPC246166
0.6835	Remote Similarity	NPC175870
0.6832	Remote Similarity	NPC473497
0.6832	Remote Similarity	NPC475413
0.6832	Remote Similarity	NPC474303
0.6831	Remote Similarity	NPC275170
0.6831	Remote Similarity	NPC473300
0.6831	Remote Similarity	NPC453583
0.6831	Remote Similarity	NPC324251
0.6831	Remote Similarity	NPC471754
0.6831	Remote Similarity	NPC306001
0.6831	Remote Similarity	NPC317882
0.6831	Remote Similarity	NPC206211
0.6831	Remote Similarity	NPC475336
0.6831	Remote Similarity	NPC471629
0.6831	Remote Similarity	NPC473400
0.6829	Remote Similarity	NPC477737
0.6829	Remote Similarity	NPC170668
0.6828	Remote Similarity	NPC474363
0.6818	Remote Similarity	NPC472413
0.6818	Remote Similarity	NPC316553
0.6813	Remote Similarity	NPC239770
0.6807	Remote Similarity	NPC477101
0.6807	Remote Similarity	NPC477097
0.6807	Remote Similarity	NPC477099
0.6806	Remote Similarity	NPC477250
0.6797	Remote Similarity	NPC79608
0.6788	Remote Similarity	NPC205389
0.6788	Remote Similarity	NPC201692
0.6776	Remote Similarity	NPC471466
0.6752	Remote Similarity	NPC108553
0.6738	Remote Similarity	NPC208553
0.6738	Remote Similarity	NPC181964
0.6738	Remote Similarity	NPC471606
0.6733	Remote Similarity	NPC80150
0.6733	Remote Similarity	NPC190663
0.6731	Remote Similarity	NPC262819
0.673	Remote Similarity	NPC232888
0.673	Remote Similarity	NPC477367
0.6711	Remote Similarity	NPC472415
0.671	Remote Similarity	NPC71271
0.6709	Remote Similarity	NPC144257
0.6707	Remote Similarity	NPC25484
0.6707	Remote Similarity	NPC135121
0.6707	Remote Similarity	NPC4108
0.6707	Remote Similarity	NPC232583
0.6702	Remote Similarity	NPC473558
0.669	Remote Similarity	NPC474314
0.6688	Remote Similarity	NPC328997
0.6688	Remote Similarity	NPC476033
0.6688	Remote Similarity	NPC294050
0.6688	Remote Similarity	NPC17567
0.6688	Remote Similarity	NPC42423
0.6687	Remote Similarity	NPC217673
0.6687	Remote Similarity	NPC52523
0.6686	Remote Similarity	NPC477098
0.6686	Remote Similarity	NPC477100
0.6685	Remote Similarity	NPC471623
0.6684	Remote Similarity	NPC191193
0.6684	Remote Similarity	NPC242662
0.6684	Remote Similarity	NPC215892
0.6684	Remote Similarity	NPC321072
0.6667	Remote Similarity	NPC136994
0.6667	Remote Similarity	NPC173934
0.6667	Remote Similarity	NPC101043
0.6667	Remote Similarity	NPC88255
0.6667	Remote Similarity	NPC107571
0.6667	Remote Similarity	NPC471103
0.6667	Remote Similarity	NPC470764
0.6667	Remote Similarity	NPC306799
0.6667	Remote Similarity	NPC477368
0.6647	Remote Similarity	NPC473670
0.6647	Remote Similarity	NPC21410
0.6647	Remote Similarity	NPC162104
0.6646	Remote Similarity	NPC86772
0.6646	Remote Similarity	NPC27721
0.663	Remote Similarity	NPC469973
0.6628	Remote Similarity	NPC156348
0.6627	Remote Similarity	NPC32197
0.6626	Remote Similarity	NPC242355
0.6625	Remote Similarity	NPC474659
0.6624	Remote Similarity	NPC272946
0.6623	Remote Similarity	NPC478015
0.6623	Remote Similarity	NPC478014
0.6623	Remote Similarity	NPC478016
0.6621	Remote Similarity	NPC477247
0.6614	Remote Similarity	NPC473490
0.6611	Remote Similarity	NPC313708
0.6609	Remote Similarity	NPC71205
0.6607	Remote Similarity	NPC469425
0.6606	Remote Similarity	NPC110305
0.6605	Remote Similarity	NPC325805
0.6605	Remote Similarity	NPC272523
0.6604	Remote Similarity	NPC477364
0.6603	Remote Similarity	NPC477370
0.6603	Remote Similarity	NPC165726
0.6603	Remote Similarity	NPC213969
0.6601	Remote Similarity	NPC139171
0.6599	Remote Similarity	NPC1986
0.6599	Remote Similarity	NPC474544
0.6597	Remote Similarity	NPC472391
0.6597	Remote Similarity	NPC475282
0.659	Remote Similarity	NPC67080
0.6588	Remote Similarity	NPC474620
0.6585	Remote Similarity	NPC477217
0.6585	Remote Similarity	NPC201244
0.6584	Remote Similarity	NPC202729
0.6581	Remote Similarity	NPC278097
0.657	Remote Similarity	NPC471203
0.6568	Remote Similarity	NPC51602
0.6566	Remote Similarity	NPC127857
0.6562	Remote Similarity	NPC311492
0.6562	Remote Similarity	NPC28836
0.6561	Remote Similarity	NPC469930
0.6558	Remote Similarity	NPC472704
0.655	Remote Similarity	NPC155329
0.655	Remote Similarity	NPC259144
0.655	Remote Similarity	NPC474219
0.655	Remote Similarity	NPC212699
0.655	Remote Similarity	NPC207675
0.655	Remote Similarity	NPC114357
0.655	Remote Similarity	NPC474378
0.655	Remote Similarity	NPC251139
0.6548	Remote Similarity	NPC60509
0.6548	Remote Similarity	NPC81698
0.6548	Remote Similarity	NPC250046
0.6548	Remote Similarity	NPC229264
0.6545	Remote Similarity	NPC262216
0.6545	Remote Similarity	NPC472375
0.6545	Remote Similarity	NPC472392
0.6543	Remote Similarity	NPC471316
0.6543	Remote Similarity	NPC473268
0.6541	Remote Similarity	NPC233692
0.6541	Remote Similarity	NPC239358
0.6538	Remote Similarity	NPC477365
0.6538	Remote Similarity	NPC472706
0.6536	Remote Similarity	NPC477115
0.6534	Remote Similarity	NPC101207
0.6531	Remote Similarity	NPC161611
0.6524	Remote Similarity	NPC477408
0.6522	Remote Similarity	NPC265459
0.6522	Remote Similarity	NPC290833
0.6522	Remote Similarity	NPC475262
0.6522	Remote Similarity	NPC23894
0.6522	Remote Similarity	NPC200154
0.6522	Remote Similarity	NPC79699
0.6516	Remote Similarity	NPC477248
0.6516	Remote Similarity	NPC472414
0.6516	Remote Similarity	NPC477249
0.6516	Remote Similarity	NPC47667
0.6514	Remote Similarity	NPC15506
0.6513	Remote Similarity	NPC243059
0.6513	Remote Similarity	NPC280827
0.6512	Remote Similarity	NPC106895
0.6512	Remote Similarity	NPC11410
0.651	Remote Similarity	NPC210531
0.651	Remote Similarity	NPC471616
0.6509	Remote Similarity	NPC165260
0.6509	Remote Similarity	NPC7095
0.6509	Remote Similarity	NPC198455
0.6509	Remote Similarity	NPC161239
0.6503	Remote Similarity	NPC67349
0.6503	Remote Similarity	NPC475195

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC185404 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	148
0.1-0.2	539
0.2-0.3	1201
0.3-0.4	2508
0.4-0.5	3112
0.5-0.6	1496
0.6-0.7	146
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6914	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD2067	Discontinued
0.6839	Remote Similarity	NPD4738	Phase 2
0.6815	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7972	Discontinued
0.674	Remote Similarity	NPD8407	Phase 2
0.6738	Remote Similarity	NPD8485	Approved
0.6704	Remote Similarity	NPD3823	Discontinued
0.6685	Remote Similarity	NPD8435	Approved
0.6685	Remote Similarity	NPD8360	Approved
0.6685	Remote Similarity	NPD8361	Approved
0.6667	Remote Similarity	NPD5030	Phase 2
0.6667	Remote Similarity	NPD8368	Discontinued
0.6646	Remote Similarity	NPD2575	Approved
0.6632	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5034	Approved
0.663	Remote Similarity	NPD5028	Approved
0.663	Remote Similarity	NPD5026	Approved
0.663	Remote Similarity	NPD36	Approved
0.663	Remote Similarity	NPD4955	Approved
0.663	Remote Similarity	NPD4954	Approved
0.6579	Remote Similarity	NPD7565	Approved
0.6576	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5036	Approved
0.6503	Remote Similarity	NPD5035	Approved
0.6497	Remote Similarity	NPD3662	Phase 3
0.6497	Remote Similarity	NPD3664	Approved
0.6497	Remote Similarity	NPD3663	Approved
0.6497	Remote Similarity	NPD3661	Approved
0.6486	Remote Similarity	NPD5038	Approved
0.6486	Remote Similarity	NPD5037	Approved
0.6474	Remote Similarity	NPD2625	Approved
0.6474	Remote Similarity	NPD2626	Approved
0.6474	Remote Similarity	NPD2160	Approved
0.6474	Remote Similarity	NPD2627	Approved
0.6474	Remote Similarity	NPD2159	Approved
0.6474	Remote Similarity	NPD2628	Approved
0.6452	Remote Similarity	NPD5159	Phase 2
0.6452	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5157	Phase 1
0.6425	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.642	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6325	Discontinued
0.6398	Remote Similarity	NPD8265	Approved
0.6392	Remote Similarity	NPD5204	Approved
0.6391	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD2217	Approved
0.6382	Remote Similarity	NPD2218	Phase 2
0.6352	Remote Similarity	NPD4620	Approved
0.6352	Remote Similarity	NPD4617	Approved
0.6352	Remote Similarity	NPD5203	Approved
0.6352	Remote Similarity	NPD5201	Approved
0.6349	Remote Similarity	NPD3819	Phase 2
0.6344	Remote Similarity	NPD3153	Approved
0.6344	Remote Similarity	NPD3154	Approved
0.6319	Remote Similarity	NPD1237	Approved
0.6319	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4466	Phase 1
0.631	Remote Similarity	NPD8150	Discontinued
0.6296	Remote Similarity	NPD6311	Approved
0.6296	Remote Similarity	NPD6310	Approved
0.6296	Remote Similarity	NPD6309	Approved
0.6294	Remote Similarity	NPD4662	Approved
0.6294	Remote Similarity	NPD4661	Approved
0.6282	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.628	Remote Similarity	NPD2569	Approved
0.628	Remote Similarity	NPD2567	Approved
0.6273	Remote Similarity	NPD4621	Approved
0.6273	Remote Similarity	NPD4619	Approved
0.6264	Remote Similarity	NPD2163	Approved
0.6264	Remote Similarity	NPD7749	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD4106	Approved
0.6258	Remote Similarity	NPD4136	Approved
0.6258	Remote Similarity	NPD4135	Approved
0.625	Remote Similarity	NPD7874	Approved
0.625	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.625	Remote Similarity	NPD2613	Approved
0.6243	Remote Similarity	NPD3455	Phase 2
0.6243	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD5981	Approved
0.623	Remote Similarity	NPD6212	Phase 3
0.623	Remote Similarity	NPD6213	Phase 3
0.623	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6229	Remote Similarity	NPD6844	Discontinued
0.6229	Remote Similarity	NPD7029	Discontinued
0.6226	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6225	Remote Similarity	NPD8404	Phase 2
0.6225	Remote Similarity	NPD2629	Approved
0.622	Remote Similarity	NPD8172	Phase 2
0.622	Remote Similarity	NPD8173	Phase 2
0.6219	Remote Similarity	NPD7801	Approved
0.6218	Remote Similarity	NPD4216	Approved
0.6218	Remote Similarity	NPD2612	Approved
0.6218	Remote Similarity	NPD2609	Approved
0.6218	Remote Similarity	NPD3132	Approved
0.6218	Remote Similarity	NPD4807	Approved
0.6218	Remote Similarity	NPD2608	Approved
0.6218	Remote Similarity	NPD4218	Approved
0.6218	Remote Similarity	NPD6287	Discontinued
0.6218	Remote Similarity	NPD4215	Approved
0.6218	Remote Similarity	NPD4217	Approved
0.6218	Remote Similarity	NPD4806	Approved
0.6218	Remote Similarity	NPD2611	Approved
0.6218	Remote Similarity	NPD3131	Approved
0.6218	Remote Similarity	NPD2610	Approved
0.6216	Remote Similarity	NPD5031	Approved
0.6216	Remote Similarity	NPD5027	Approved
0.6216	Remote Similarity	NPD5029	Approved
0.6207	Remote Similarity	NPD4380	Phase 2
0.6203	Remote Similarity	NPD5667	Approved
0.6198	Remote Similarity	NPD6535	Approved
0.6198	Remote Similarity	NPD6534	Approved
0.6196	Remote Similarity	NPD5119	Approved
0.6196	Remote Similarity	NPD5120	Approved
0.6196	Remote Similarity	NPD5121	Approved
0.6194	Remote Similarity	NPD5306	Approved
0.6194	Remote Similarity	NPD5305	Approved
0.6193	Remote Similarity	NPD7460	Discontinued
0.6188	Remote Similarity	NPD8462	Phase 1
0.6185	Remote Similarity	NPD7239	Suspended
0.6183	Remote Similarity	NPD5032	Approved
0.618	Remote Similarity	NPD7075	Discontinued
0.6176	Remote Similarity	NPD7236	Approved
0.6174	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD7978	Discontinued
0.6168	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD2652	Approved
0.6159	Remote Similarity	NPD7113	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD2650	Approved
0.6158	Remote Similarity	NPD6836	Approved
0.6158	Remote Similarity	NPD5402	Approved
0.6154	Remote Similarity	NPD3400	Discontinued
0.6149	Remote Similarity	NPD2649	Approved
0.6149	Remote Similarity	NPD2651	Approved
0.6136	Remote Similarity	NPD6801	Discontinued
0.6135	Remote Similarity	NPD4746	Phase 3
0.6135	Remote Similarity	NPD2573	Approved
0.6135	Remote Similarity	NPD3615	Approved
0.6135	Remote Similarity	NPD3616	Approved
0.6135	Remote Similarity	NPD2571	Approved
0.6135	Remote Similarity	NPD2574	Discontinued
0.6135	Remote Similarity	NPD3614	Approved
0.6135	Remote Similarity	NPD3088	Approved
0.6135	Remote Similarity	NPD2570	Approved
0.6135	Remote Similarity	NPD3087	Approved
0.6135	Remote Similarity	NPD3090	Approved
0.6135	Remote Similarity	NPD4745	Approved
0.6135	Remote Similarity	NPD2566	Approved
0.6135	Remote Similarity	NPD3089	Approved
0.6135	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD2424	Discontinued
0.6129	Remote Similarity	NPD4105	Approved
0.6129	Remote Similarity	NPD4102	Approved
0.6127	Remote Similarity	NPD5403	Approved
0.6124	Remote Similarity	NPD3882	Suspended
0.6122	Remote Similarity	NPD6781	Approved
0.6122	Remote Similarity	NPD6778	Approved
0.6122	Remote Similarity	NPD6780	Approved
0.6122	Remote Similarity	NPD6779	Approved
0.6122	Remote Similarity	NPD4914	Approved
0.6122	Remote Similarity	NPD6782	Approved
0.6122	Remote Similarity	NPD6777	Approved
0.6122	Remote Similarity	NPD6776	Approved
0.6118	Remote Similarity	NPD6190	Approved
0.6114	Remote Similarity	NPD8417	Discontinued
0.6111	Remote Similarity	NPD6039	Approved
0.6108	Remote Similarity	NPD5712	Approved
0.6103	Remote Similarity	NPD7700	Phase 2
0.6103	Remote Similarity	NPD7699	Phase 2
0.6102	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.609	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD7799	Discontinued
0.6082	Remote Similarity	NPD3300	Phase 2
0.608	Remote Similarity	NPD8320	Phase 1
0.608	Remote Similarity	NPD3067	Approved
0.608	Remote Similarity	NPD8319	Approved
0.6078	Remote Similarity	NPD1348	Approved
0.6071	Remote Similarity	NPD4152	Approved
0.6069	Remote Similarity	NPD7613	Discontinued
0.6067	Remote Similarity	NPD7318	Phase 3
0.6061	Remote Similarity	NPD4685	Phase 3
0.6061	Remote Similarity	NPD4684	Phase 3
0.6061	Remote Similarity	NPD6823	Phase 2
0.6061	Remote Similarity	NPD4686	Approved
0.6061	Remote Similarity	NPD6863	Phase 2
0.6059	Remote Similarity	NPD4628	Phase 3
0.6053	Remote Similarity	NPD3863	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD8434	Phase 2
0.6047	Remote Similarity	NPD6799	Approved
0.6043	Remote Similarity	NPD6104	Discontinued
0.6042	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.604	Remote Similarity	NPD2182	Approved
0.6037	Remote Similarity	NPD7713	Phase 3
0.6036	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6027	Remote Similarity	NPD6647	Phase 2
0.6026	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6026	Remote Similarity	NPD969	Suspended

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data